Water → 4-(4-Phenylbutoxy)styrene

HRID 1603927ノート

反応式

HRID 1603927 の反応式
[CH2:1]([Li])CCC.[C:6]1([CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.O.C(OCC)C>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1.CCCCCC>[C:6]1([CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:24]=[CH:23][C:20]([CH:21]=[CH2:1])=[CH:19][CH:18]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

参加物

8

反応物 4

HCID 962WaterHCID 3283Diethyl EtherHCID 158710154-(4-Phenylbutoxy)benzaldehydeHCID 178418339Butyllithium

生成物 1

HCID 196062504-(4-Phenylbutoxy)styrene収率 62%

試薬・触媒・溶媒 3

HCID 74505Methyltriphenyliphosphonium bromide触媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
0 °C

実験手順

A solution of methyltriphenylphosphonium bromide (4.98 g, 13.9 mmol) in anhydrous tetrahydrofuran (130 ml) at 0° C. and under inert atmosphere was added with a 1.6M butyl lithium solution in hexane (8.69 ml) and the mixture was left under stirring at 0° C. for 2 h. After that, a solution of 4-(4-phenylbutoxy)benzaldehyde (2.5 g, 9.84 mmol) in tetrahydrofuran (10 ml) was added and the mixture was left under stirring at room temperature for 36 h, then carefully added with water (20 ml) and extracted with ethyl ether (4×50 ml). The organic extracts were dried and the solvents were evaporated off under reduced pressure. The resulting crude was purified by chromatography through a silica gel column, eluting with petroleum ether:ethyl ether, 95:5, thereby recovering 4.20 g of the title compound (62% yield).

後処理

  1. waitthe mixture was left
  2. waitthe mixture was left
  3. stirringunder stirring at room temperature for 36 h
  4. extractionextracted with ethyl ether (4×50 ml)
  5. customThe organic extracts were dried
  6. customthe solvents were evaporated off under reduced pressure
  7. customThe resulting crude was purified by chromatography through a silica gel column
  8. washeluting with petroleum ether

出典と根拠

ORDレコード
ord-8d51799efc6a428b910662c3291a4696
出典データセット
uspto-grants-1999_11
特許番号
US05990142

反応ノート

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